US4924007A - Process for the preparation of cyclic sulphates - Google Patents

Process for the preparation of cyclic sulphates Download PDF

Info

Publication number
US4924007A
US4924007A US07/351,831 US35183189A US4924007A US 4924007 A US4924007 A US 4924007A US 35183189 A US35183189 A US 35183189A US 4924007 A US4924007 A US 4924007A
Authority
US
United States
Prior art keywords
radicals
alkyl
aryloxy
alkoxy
process according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
US07/351,831
Other languages
English (en)
Inventor
Viviane Massonneau
Michel Mulhauser
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhone Poulenc Sante SA
Original Assignee
Rhone Poulenc Sante SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhone Poulenc Sante SA filed Critical Rhone Poulenc Sante SA
Assigned to RHONE-POULENC SANTE, A FRENCH BODY CORP. reassignment RHONE-POULENC SANTE, A FRENCH BODY CORP. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: MASSONNEAU, VIVIANE, MULHAUSER, MICHEL
Application granted granted Critical
Publication of US4924007A publication Critical patent/US4924007A/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates

Definitions

  • the present invention relates to the preparation of cyclic sulphates of general formula: ##STR3## in which the substituents R 1 , R 2 , R 3 , R 4 , R 5 and R 6 , which are identical or different, denote a hydrogen or halogen atom or an alkyl, aryl, alkoxy, aryloxy or alkoxycarbonyl radical and n is equal to 0 or 1.
  • alkyl radicals and the alkyl moieties of the alkoxy or alkoxycarbonyl radicals contain 1 to 4 carbon atoms each and may be optionally substituted by one or more identical or different atoms or radicals chosen from halogen atoms and alkoxy, aryloxy or alkoxycarbonyl radicals,
  • aryl radicals and the aryl moieties of the aryloxy radicals contain 6 to 10 carbon atoms each and may be optionally substituted by one or more identical or different atoms or radicals chosen from halogen atoms and alkyl, alkoxy, aryloxy or alkoxycarbonyl radicals.
  • the present invention relates to the preparation of cyclic sulphates of general formula (I) in which n is equal to 0 or 1 and the symbols R 1 , R 2 , R 3 , R 4 , R 5 and R 6 , which are identical or different, denote a hydrogen atom or an alkyl radical.
  • the sulphates of general formula (I) are intermediates which can be employed in organic chemistry, in particular to perform hydroxyethylation reactions.
  • German Patent DE No. 1,049,870 it is known to prepare ethylene sulphate by heating a mixture of ethylene glycol, sulphuric acid and an excess of thionyl chloride under reflux for 50 hours.
  • cyclic sulphates of general formula (I) may be obtained by a simple and inexpensive process which consists in rapidly reacting, at a temperature of between 150° and 250° C., concentrated sulphuric acid with a glycol of general formula: ##STR4## in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are defined as above.
  • the glycol of formula II and the concentrated sulphuric acid in the liquid or, preferably, the vapour phase are kept in contact at the reaction temperature in the range 150° to 250° C. for no more than one hour, preferably from less than 1 second to 30 minutes.
  • the cyclic sulphate of general formula (I) is trapped by cooling (i.e. by condensation from the vapour phase) or by dissolving it in a suitable solvent.
  • a substantially equimolar mixture of glycol of general formula (II) and of concentrated sulphuric acid is generally employed.
  • the process is preferably carried out under a reduced pressure, generally in the region of 1 mm Hg (0.13 kPa), and in the vapour phase.
  • the process may be carried out by rapidly passing the mixture of concentrated sulphuric acid and of glycol of general formula (II) through a tubular reactor heated to a temperature of between 150° and 250° C. and kept under reduced pressure.
  • the mixture (2.5 g) is introduced with a syringe into the reactor shown in the accompanying FIG. 1.
  • the reactor is heated to 200° C. by means of a heating tape.
  • the apparatus is placed under a reduced pressure of 1 mm Hg (0.13 kPa).
  • the residence time of the ethylene glycol sulphuric acid mixture in the heated part of the reactor is 10 minutes.
  • ethylene sulphate formed is collected in the Vigreux column placed in a jacket containing solid CO 2 .
  • the Vigreux column is rinsed with dichloromethane.
  • ethylene sulphate (0.85 g) is obtained in the form of white crystals.
  • the yield is 45% based on the sulphuric acid employed.
  • FIG. 1

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Detergent Compositions (AREA)
  • Lubricants (AREA)
  • Coloring (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Saccharide Compounds (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
US07/351,831 1988-05-16 1989-05-15 Process for the preparation of cyclic sulphates Expired - Fee Related US4924007A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8806523A FR2631340B1 (fr) 1988-05-16 1988-05-16 Procede de preparation de sulfates cycliques
FR8806523 1988-05-16

Publications (1)

Publication Number Publication Date
US4924007A true US4924007A (en) 1990-05-08

Family

ID=9366323

Family Applications (1)

Application Number Title Priority Date Filing Date
US07/351,831 Expired - Fee Related US4924007A (en) 1988-05-16 1989-05-15 Process for the preparation of cyclic sulphates

Country Status (20)

Country Link
US (1) US4924007A (fr)
EP (1) EP0343053B1 (fr)
JP (1) JPH0217183A (fr)
KR (1) KR900018067A (fr)
CN (1) CN1037708A (fr)
AT (1) ATE71943T1 (fr)
AU (1) AU618092B2 (fr)
CA (1) CA1305712C (fr)
DE (1) DE68900749D1 (fr)
DK (1) DK238289A (fr)
ES (1) ES2028455T3 (fr)
FI (1) FI892327A (fr)
FR (1) FR2631340B1 (fr)
GR (1) GR3003629T3 (fr)
HU (1) HU201542B (fr)
IL (1) IL90306A0 (fr)
PT (1) PT90573B (fr)
SU (1) SU1657063A3 (fr)
YU (1) YU46933B (fr)
ZA (1) ZA893620B (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5149844A (en) * 1989-10-20 1992-09-22 Air Products And Chemicals, Inc. Heterocyclic diorganotin catalysts for use in polyurethane systems
US5171892A (en) * 1991-07-02 1992-12-15 E. I. Du Pont De Nemours And Company Chiral phospholanes via chiral 1,4-diol cyclic sulfates
US5274123A (en) * 1990-07-09 1993-12-28 Rhone-Poulenc Rorer, S.A. Process for the preparation of cyclic sulphates
US6180799B1 (en) * 2000-05-01 2001-01-30 The United States Of America As Represented By The Secretary Of The Air Force Sulfalation of tetraol
US8247526B2 (en) 2010-12-20 2012-08-21 E I Du Pont De Nemours And Company Process for the preparation of polyalkylene ether glycol
CN114656444A (zh) * 2022-03-04 2022-06-24 河北松辰医药科技有限公司 一种2,2-二氟-1,3-丙基磺酸内酯的合成方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107353277B (zh) * 2017-07-11 2020-01-31 湖南有色郴州氟化学有限公司 一种环状硫酸酯的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1171347A (fr) * 1956-10-24 1959-01-23 Wolfen Filmfab Veb Procédé de préparation de sulfates d'alcènes ou d'oléfines

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1049870B (de) * 1959-02-05 VEB Filmfabrik AGFA Wolfen, Wolfen (Kr. Bitterfeld) Verfahren zur Herstellung von cyclischen Schwcfelsäureestern diprimärer Glykole
FR2628423B1 (fr) * 1988-03-08 1991-09-13 Rhone Poulenc Sante Procede de preparation de sulfates cycliques

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1171347A (fr) * 1956-10-24 1959-01-23 Wolfen Filmfab Veb Procédé de préparation de sulfates d'alcènes ou d'oléfines

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Lictenberger et al., Bull. Soc. Chim. (France), 1948, pp. 1002 1012. *
Lictenberger et al., Bull. Soc. Chim. (France), 1948, pp. 1002-1012.

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5149844A (en) * 1989-10-20 1992-09-22 Air Products And Chemicals, Inc. Heterocyclic diorganotin catalysts for use in polyurethane systems
US5274123A (en) * 1990-07-09 1993-12-28 Rhone-Poulenc Rorer, S.A. Process for the preparation of cyclic sulphates
US5171892A (en) * 1991-07-02 1992-12-15 E. I. Du Pont De Nemours And Company Chiral phospholanes via chiral 1,4-diol cyclic sulfates
US5329015A (en) * 1991-07-02 1994-07-12 E. I. Du Pont De Nemours And Company Chiral phospholanes via chiral 1,4-diol cyclic sulfates
US5532395A (en) * 1991-07-02 1996-07-02 E. I. Du Pont De Nemours And Company Chiral phospholanes via chiral 1,4-diol cyclic sulfates
US5559267A (en) * 1991-07-02 1996-09-24 E. I. Du Pont De Nemours And Company Hydrogenation process using catalysts made from chiral phospholanes via chiral 1,4-diol cyclic sulfates
US5565593A (en) * 1991-07-02 1996-10-15 E. I. Du Pont De Nemours And Company Chiral phospholanes via chiral 1,4-diol cyclic sulfates
US5596114A (en) * 1991-07-02 1997-01-21 E. I. Du Pont De Nemours And Company Chiral phospholanes via chiral 1 4-diol cyclic sulfates
US6180799B1 (en) * 2000-05-01 2001-01-30 The United States Of America As Represented By The Secretary Of The Air Force Sulfalation of tetraol
US8247526B2 (en) 2010-12-20 2012-08-21 E I Du Pont De Nemours And Company Process for the preparation of polyalkylene ether glycol
CN114656444A (zh) * 2022-03-04 2022-06-24 河北松辰医药科技有限公司 一种2,2-二氟-1,3-丙基磺酸内酯的合成方法

Also Published As

Publication number Publication date
EP0343053A1 (fr) 1989-11-23
AU618092B2 (en) 1991-12-12
SU1657063A3 (ru) 1991-06-15
YU99389A (en) 1990-06-30
HU201542B (en) 1990-11-28
FI892327A0 (fi) 1989-05-15
ZA893620B (en) 1990-01-31
EP0343053B1 (fr) 1992-01-22
AU3479589A (en) 1989-11-16
FR2631340B1 (fr) 1990-07-27
FI892327A (fi) 1989-11-17
FR2631340A1 (fr) 1989-11-17
ATE71943T1 (de) 1992-02-15
CA1305712C (fr) 1992-07-28
PT90573A (pt) 1989-11-30
YU46933B (sh) 1994-06-24
DE68900749D1 (de) 1992-03-05
KR900018067A (ko) 1990-12-20
JPH0217183A (ja) 1990-01-22
DK238289D0 (da) 1989-05-16
GR3003629T3 (fr) 1993-03-16
DK238289A (da) 1989-11-17
CN1037708A (zh) 1989-12-06
PT90573B (pt) 1994-08-31
IL90306A0 (en) 1989-12-15
ES2028455T3 (es) 1992-07-01

Similar Documents

Publication Publication Date Title
US4924007A (en) Process for the preparation of cyclic sulphates
US4764309A (en) Preparation of chlorocarboxylic acid chlorides
KR870001929B1 (ko) 1,3-디알킬-2-이미다졸리디논의 제조방법
NZ234482A (en) Removal of isocyanic acid from an ammonia-containing gas
EP0302195B1 (fr) Procédé de préparation de naphtacènes
EP0147472B1 (fr) 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one
CA1313191C (fr) Procede pour la production d'oximosilanes
JPS5810582A (ja) スピロオルトカ−ボネ−トの製造法
Jurczak et al. Synthesis of N, N′-dimethyl diazacoronands via double-quaternization reaction
US5648537A (en) Process for the synthesis of substituted carbodiimides
US4331817A (en) Process for the preparation of 4-arylthioanilines
US4282364A (en) Process for the preparation of thiazoles
EP0143768B1 (fr) Préparation d'ortho-(alkylthiométhyl)anilines par réarrangement catalytique de sulfimides
Davies et al. Intramolecular cyclisation of 2-phenylethyl isocyanates
US4305889A (en) Process for producing α, α, α-trifluoro-o-toluic fluoride
US4558161A (en) Process for preparing halo-substituted diarylsulfones
EP0039166A1 (fr) Procédé pour la préparation en continu de dichloroacétamides
KR100315053B1 (ko) 트리플루오로아세트산 테트라알킬플루오로 포름아미디늄 및 그의 제조방법
KR900007314B1 (ko) N-(메톡시아세틸)-n-(2,6-디메틸페닐)-3-아미노-옥사조리딘-2-온의 제조방법
KR820001181B1 (ko) 벤젠 포스포닉 디할라이드의 제조방법
SU1293179A1 (ru) Способ получени 1,2-бис-(3,5-диоксопиперазин-1-ил)-алканов
US5097055A (en) Production of methylphenyltrisiloxane
KR101090539B1 (ko) 시클로알킬-히드라진의 엑소시클릭 유도체 및헤테로시클로알킬-히드라진의 엑소시클릭 유도체의합성방법
EP0163948B1 (fr) Procédé pour la préparation d'une indoline
IL132077A (en) Process for the production of 1-chlorocarbonyl-4-piperidinopipridine or its hydrochloride

Legal Events

Date Code Title Description
AS Assignment

Owner name: RHONE-POULENC SANTE, 20 AVENUE RAYMOND ARON, 92160

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:MASSONNEAU, VIVIANE;MULHAUSER, MICHEL;REEL/FRAME:005083/0387

Effective date: 19890509

LAPS Lapse for failure to pay maintenance fees
FP Lapsed due to failure to pay maintenance fee

Effective date: 19940511

STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362